Cyanocobalamin

• Catalog No.: DB00115
• CAS Number: 68-19-9
• M. F.: C63H88CoN14O14P
• M. W.: 1355.365181

SYNONYMS

• IUPAC name: cyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-(2-{[(2R)-2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1H-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl]carbamoyl}ethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
• IUPAC Traditional name: cyano[(1R,2R,3R,4R,6Z,8S,11Z,13S,14S,16Z,18S,19S)-8,13,18-tris(2-carbamoylethyl)-3,14,19-tris(carbamoylmethyl)-4-(2-{[(2R)-2-{[(2R,3S,4R,5S)-5-(5,6-dimethyl-1,3-benzodiazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl phosphonato]oxy}propyl]carbamoyl}ethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1?,?.1?,??.1??,??]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
• Brand Name: Depinar; Vitabee 12; Redisol; M.V.I. Pediatric; Rubratope-60 Kit; Bedoz; Cyomin; Nascobal; Cobolin-M; Crysti-12; Primabalt; Rubivite; Rubratope-57 Kit; Shovite; Vi-Twel; Vibal; Vibisone; Dicopac; Rubramin PC; Anacobin; Berocca PN; Berubigen; Betalin 12; Cernevit-12; Cobavite; Cobex; Crystamine; Cyanocobalamin Co 57 Schilling Test Kit; Cyanoject; Dicopac Kit; Neuroforte-R; Ruvite; Vitaped
• Synonyms: Vitamin B12; Vitamin B12 complex; Cyanocob(III)alamin; Vitamine B12

DATABASE IDS

• PubChem CID: 44176380
• PubChem SID: 46509031
• CAS Number: 68-19-9

PROPERTIES

• Solubility: 12.5 mg/mL [MERCK INDEX (1996)]

DETAILS

Description (English)

• Drug Groups: approved; nutraceutical
• Description: Cyanocobalamin (commonly known as Vitamin B12) is the most chemically complex of all the vitamins. Cyanocobalamin's structure is based on a corrin ring, which, although similar to the porphyrin ring found in heme, chlorophyll, and cytochrome, has two of the pyrrole rings directly bonded. The central metal ion is Co (cobalt). Cyanocobalamin cannot be made by plants or by animals, as the only type of organisms that have the enzymes required for the synthesis of cyanocobalamin are bacteria and archaea. Higher plants do not concentrate cyanocobalamin from the soil and so are a poor source of the substance as compared with animal tissues. Cyanocobalamin is naturally found in foods including meat (especially liver and shellfish), eggs, and milk products. [HMDB]
• Indication: For treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.
• Pharmacology: Cyanocobalamin (Vitamin B12) is a water-soluble organometallic compound with a trivalent cobalt ion bound inside a corrin ring. It is needed for nerve cells and red blood cells, and to make DNA. Vitamin B12 deficiency is the cause of several forms of anemia.
• Toxicity: Anaphylactic reaction (skin rash, itching, wheezing)-after parenteral administration. ORL-MUS LD₅₀ > 8000 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Readily absorbed in the lower half of the ileum.
• Half Life: Approximately 6 days (400 days in the liver).
• Protein Binding: Very high (to specific plasma proteins called transcobalamins); binding of hydroxocobalamin is slightly higher than cyanocobalamin.
• References: Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. [Pubmed] ; Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. [Pubmed] ; Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. [Pubmed] ; Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. [Pubmed] ; Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Wickramasinghe SN: Morphology, biology and biochemistry of cobalamin- and folate-deficient bone marrow cells. Baillieres Clin Haematol. 1995 Sep;8(3):441-59. Pubmed
• Sharabi A, Cohen E, Sulkes J, Garty M: Replacement therapy for vitamin B12 deficiency: comparison between the sublingual and oral route. Br J Clin Pharmacol. 2003 Dec;56(6):635-8. Pubmed
• Hall AH, Rumack BH: Hydroxycobalamin/sodium thiosulfate as a cyanide antidote. J Emerg Med. 1987;5(2):115-21. Pubmed
• Andres E, Noel E, Goichot B: Metformin-associated vitamin B12 deficiency. Arch Intern Med. 2002 Oct 28;162(19):2251-2. Pubmed
• Gilligan MA: Metformin and vitamin B12 deficiency. Arch Intern Med. 2002 Feb 25;162(4):484-5. Pubmed